Paternity Leave & Letting Things Run

Borrowed

"You’ll also be transformational, not transactional, in all decisions you make. For example, when you decide to take the day off work to spend time with your family, you won’t see that as a cost. You’ll focus on the investment you’re making in your loved ones. By shifting your focus from cost to investment, you stop worrying about what you’re giving up and instead realize that by making powerful decisions you can make enormous gains."

From "Who Not How" by Dan Sullivan, Benjamin Hardy [Book]

Learned

I’ve been on paternity leave since the holidays. It’s been special having this time at home with the family. Our routine is a bit sideways. Cora has good nights and bad nights. Of course, sleep is unpredictable. And I'm enjoying all sorts of home projects and baby snuggles. The days blur together a bit, but I wouldn’t change any of it. Times like this pass just as quickly as they arrive.

I think back to a time many years ago when the idea of taking an extended leave was unsettling. I was just a Senior Designer! Yet, the team seemed lost without me. They told me so. At the time, I framed that as responsibility, even as proof that I was doing something right. Deep down, there was something validating about believing things might stall or fall apart while I was away.

I took that vacation anyway, and I’m so glad I did. Dana and I went on an 11-day trip to Thailand. It was our first time traveling together, and we chose a place that took nearly 24 hours to get to. Luckily, we had a blast.

Over time, I’ve learned that being indispensable isn’t something to strive for. It’s usually a sign that you’re too central to the system. And systems like that struggle to grow. They don’t scale well, and they quietly create pressure for everyone involved, even when things appear to be working.

Coming into leave as CEO, I was wondering how I’d feel, but as it got closer, I felt at ease, not worried that everything would crumble in my absence. It’s been encouraging to see the team operate confidently without me hovering. This weekend is the NRF conference in New York. There was a time when if I couldn’t make it, Barrel simply wasn’t there. This year, our Growth Team is representing Barrel, meeting partners, attending events, and hosting one of our own. Sure, I wish I were there to spend time together, but watching others step into that role feels like a win and a reminder of what happens when you let go.

I didn’t do any major preparation before stepping away. There was no elaborate handoff document or plan. Instead, I focused on making sure people felt clear and had what they needed from me. Part of that was keeping our existing rituals intact. Weekly meetings, standing check-ins, and the cadence we’ve built only work if they continue, whether I’m there or not. If they waver in my absence, the habit breaks. I also asked my direct reports on the Growth and Leadership teams to send a brief weekly update email.

The format is simple, broken into four parts:

• Updates on progress, wins, and what’s happened since last Friday
• Areas where perspective, advice, or ideas would be helpful
• Priority topics or challenges that matter most right now
• Plans, decisions, and commitments moving forward

Rather than trying to check in everywhere or feeling disconnected, this creates leverage. It gives me a clear window into what actually matters and where my input is useful, without pulling me back into the day-to-day.

Paternity leave or not, I’ve found there’s often a lot to learn when something pulls you out of the regular rhythm of what’s become comfortable. I haven't been out long, but I can already see the value in the weekly brief, making things this clear and concise. When progress, risk, and priorities are visible, they stop living in one person’s head. The business becomes easier to understand, easier to support, and easier to step away from when life calls for it.

Thought

Where am I still equating being needed with being effective?